


Spades Slick: Make Him Pay

by Path



Series: Midnight City Stories [15]
Category: Homestuck, MS Paint Adventures, Problem Sleuth (Webcomic)
Genre: Humiliation, M/M
Language: English
Status: Completed
Published: 2011-06-07
Updated: 2011-06-07
Packaged: 2017-10-20 05:10:34
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,918
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/209088
Author URL: https://archiveofourown.org/users/Path/pseuds/Path
Summary: <blockquote class="userstuff">
              <p>You are the infamous mobster known as Spades Slick, and you have finally cornered this know-it-all detective who keeps prying into your business. It's time to make him regret he ever stuck his nose in your business.</p>
            </blockquote>





	Spades Slick: Make Him Pay

**Author's Note:**

> For the first Kink Meme. I like going back and filling old prompts.
> 
> "How about a Problem Sleuth/Spades Slick, involving PS getting captured, tied up and humiliated by Slick. It's not quite a crossover, considering. Maybe PS is getting forced to suck Slick off at key-point?"
> 
> This was called "Satisfaction" when I posted it on LJ, but OH BOY I regret not calling it this from the start. This also sort of my prologue to the Midnight City Stories series. I imagine this is the first time these two assholes met. :P

Few things are as deeply satisfying as shoving your cock down the throat of a mortal enemy.

Sure, Problem Sleuth isn't _really_ your mortal enemy, but you're not allies, definitely not buddies, and the guy has been a thorn in your side every chance he's gotten.

But now you're getting a chance of your own, and hell, you're really enjoying it. Fine, maybe he's not struggling with quite the same vigour as Crowbar did (and oh, what a great night that was), but the idea's there, and it's more than enough. You cock his own key against his jaw, tighten your other hand in his hair, push further in and listen to him choke around you.

Yep. This is the life. But Spades Slick doesn't shoot it off in a few minutes, and one way-too-nosy detective is going to learn that sitting back and taking your time can actually be rewarding. Maybe if he'd taken his time, he wouldn't have stumbled into your warehouse when you and Boxcars were on the patrol.

You pull your dick out of his mouth and clock him with his keys, knocking his hat off. He's already on his knees, hands cuffed behind his back, so he just goes straight to the floor, catching himself on a bracing shoulder to avoid the pavement delivering a second sharp blow to his head. You walk up to him where he lies and laugh. Not that you haven't been chuckling to yourself this whole time. Nosy meddling do-gooder nearly fucking ruining everything.

"You know how much I went through to get these shipments going?" you ask him.

Problem Sleuth struggles and twists, trying to get to his knees once more. "You had to get out of bed by noon?" he mutters, slurring the words a little.

"Yeah," you answer, grinning with your mouthful of little knives. "I had to get up at 10 fucking AM to deal with this. And more importantly, I had to watch the whole time for fuckers like you looking to screw it up. I've blackmailed a dozen officials, most of the force, and set Kingpin's assholes up in a whirlwind just to keep all your little friends busy. And I still find you sticking your nose in over here."

You place your foot delicately on his jaw and push, forcing him back to the concrete. "In fact, I've been all over town these past weeks. Droog tells me I ain't getting enough sleep, and I need a break to fix myself back up." You look at your shoe on his face with an expression of mocking consideration. "Going to need these shoes cleaned soon." You take it from his face and place it right in front of his eyes. Then you pull out the ace of spades and set it gently next to his temple.

"The way I see it," you say easily, "you drive me all over town to prepare for this, you might as well deal with the clean-up."

Problem Sleuth looks up at you with no expression on his face. There's a lovely crosshatched bruise blossoming on his cheek and temple where you smacked him with his own gun. Then he looks at your shoe, grits his teeth, and spits on it.

You kick him in the ribs, and wait.

Then you laugh, and wait for him to lick the dirt off your shoes.

His jaw is set when he finally looks back up at you again, spitting a mouthful of dirt off into the warehouse. You just smile viciously at him. "Well, not bad," you say. "Clean enough for dinner at the mayor's. And hey, I've got something else for you to clean off while you're at it."

You're not done with this little sneak, and you've only been getting harder watching him grudgingly weigh savage beatings against savage humiliation. He glares up at you. He's going to break soon enough, though, and you're going to enjoy every second of it. Still steel-eyed, he stumbles to his knees, catches his breath, and raises his head.

Oh yeah. You're enjoying this.

"Hmm, oh," you say, as if it just occurred to you. You raise his jaw a little more with the ace of spades, and he flinches at the touch of the frigid iron. You look at him with some thought. "No," you say. "All you're going to do is dirty me up with that mouth. Might as well fuck a garbage can with all the crap I've walked over in the last few days. And hey, now that I mention it...."

You crack him across the shoulders with the horse hitcher. He goes straight down, face impacting with the pavement and his nose beginning to bleed across it. You put the hitcher head down right between his shoulder blades, yank down his pants, and kneel behind him, positioning.

You spit on your fingers and press two up against his ass. He lets out some strangled cry and tries to pull away, but while you were an equal match twenty minutes ago, now the cold and blood loss and bruising are starting to get to him, and you don't have much trouble keeping him down. You slide your fingers in, twisting into him, and begin scissoring them in and out, slow but sharp, and taking your time. "You know," you say to him, grinning madly, "I was planning on murdering you here. Leaving your broken bleeding cum-filled body in the middle of fucking nowhere so that by the time they found your rotting corpse, they'd need a full out inquest, really tearing your body apart."

You add a third finger. "The papers'd pick it up, and everybody in the whole fucking city would know how many holes you got fucked in before your own bullet went through your brain. Maybe they'd think you did it yourself- offed yourself in embarrassment after somebody proved they were really stronger than you." You can hear the sound of his teeth gritting together, and faintly muttered curses or moans. You can't quite tell yet; maybe it's both.

Curious, you pull your fingers out, and Problem Sleuth lets out a whimper. Yep, no mistaking that. You line yourself up behind him and begin to press yourself in. Over his grit-teeth-grinding and shaky cries, you bend yourself over, close to his ear, and speak quietly. "But now, I'm thinking I'm not gonna kill you after all. Because I can do all that, get all of that, with you still alive. I'm going to leave you here, approximately just as broken, bleeding, and full of my cum as you would be dead, and yet I get the joy of knowing _it won't be for the last time_."

You are rocking into him now, the horse hitcher like a flag planted in his back, and he is actually moaning beneath you. You throw your head back and laugh. "Because look at you, Sleuth! You're taking it in the ass from the leader of the Midnight Crew, and you're getting off on it. I gotta leave you alive now. Next time you cross me, I'll just tie you up and fuck you again, and you'll say "Thanks, Slick, can I lick your shoes off while I'm at it?"

You can't hold it back much longer. Your words are twisting, shaking and bucking like you are inside him. "Next time I'll bring Droog, too, see if he wants his cock cleaned. His shoes are nice enough already. I'll bring the whole Crew, and we'll fuck you and leave you for the cops to clean up, and we'll- we'llll- fuck-"

And then you're coming, lodged deep inside him, and he's howling on the floor in front of you into that pool of his own blood. His face is smeared with dirt and precum and red, and yours has a smile of passionate malicious joy pasted on it as you finish. To give yourself the cherry on top, you toss the horse hitcher aside and drape yourself over his body, setting your teeth into his shoulder and digging them in. You growl in relief and the taste of his blood in your teeth.

You finally pull yourself (and your fangs) out of Sleuth, wipe your fingers on his coat, and stand, getting yourself back together and retrieving your horse hitcher. You toss it in your hands once, twice, then use it to push Sleuth over. He's curled in a ball, face pained, cock rigid, hands still cuffed behind his back. You consider, then approach him again.

You toe his legs apart; he's still writhing against the floor and doesn't make a move to stop you. You place your so-shiny sole against his cock and press. Sleuth writhes in mixed pain and pleasure- mostly pain. "You know where the hideout is," you say casually, feeling his cock jumping against the bottom of your foot, "you cracked that one long ago. Why don't you come by the next time you need a good fucking, and when I'm not busy, I'll get around to you?"

Sleuth is gasping and straining against you. "I hear the Felt are always looking for someone to keep them occupied," you suggest. "Maybe me, Droog, Boxcars, Deuce, that's not enough? Why don't you show up in the Felt Manor and whore yourself out like you're doing now? Fifteen of them should be enough for you. I'm sure they'd give in if you just begged."

Sleuth's teeth grind together one last time and he finishes, spurting across his already-ruined shirt and jacket. You smirk, satisfied, and, as a last token of your esteem, toss a coin at him over your shoulder. You walk away, slinging your jacket over your shoulder, and listen to it roll on its edge and chime on the concrete.

The sound of a job well done.

= = =

Problem Sleuth finally finds the right angle to get his cuffed hands under him and around to the front, then stumbles to his feet, pulling his trousers up and fumbling with his belt.

Altogether, this was not the worst defeat he's ever suffered. Certainly it was less violent than he'd expected from Spades Slick. The fact that he wasn't dead or fucked in the eye socket seemed pretty good by comparison, really, especially considering what Slick outright said he had planned.

Sleuth gets his hands between one of the still-operating machines in the corner of the warehouse, biting the chain on his cuffs open. He shakes his arms, stretches, takes account of bruises. All told, he feels... well, beaten, shaken, and in large amounts of pain, but through that, inexplicably good.

Part of that, of course, he reasons, may be the running tape recorder in his inner jacket pocket. It will have gotten all of Slick's plans down, in his own voice, more than enough for the chief to be forced to take action. And besides his case, he doesn't feel terrible despite it all. Slick could have left him dead, or a dozen other dislikeable outcomes. It was still almost entirely dislikeable, but maybe Spades Slick isn't entirely as irredeemable as he was led to believe.

He's completely filthy and his entire body feels disgusting, but despite it, his brain is still buzzing and his limbs fuzzily comfortable. His hands free, clothed again, and with tape recorder in hand, Problem Sleuth smiles wearily at it and trudges home. He presses Play as he walks, and listens to Spades Slick incriminating himself.

The sound of a job well done.


End file.
